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    Technology

    Knuckle Up with Nakul

    Knuckle Up is about the HOW of building iconic companies. Recruiting, culture, intensity, the inner game of being a founder CEO. The stuff that actually separates great companies from good ones. Hosted by Nakul Mandan (GP, Audacious Ventures), each episode goes deep with founders who’ve done it at the highest level. Not highlight reels. Operating playbooks, straight from the best of the best.

    knuckleuphq.substack.com

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    Latest Episodes:
    How Railway says no to 90% of ideas and keeps winning | Jake Cooper (Founder, CEO) Oct 13, 2026
    Show notes

    Jake Cooper never set out to start a company. After leaving Uber in 2020, he put together a box of databases for his own side projects, kept coming back to it, and eventually posted it on Twitter asking who he should talk to about a job working on it. He got no job offers, just a few angel checks. That side project became Railway, the cloud platform now used by millions of developers, and Jake still runs it as a solo founder.

    Railway is run by around 40 people and is closing in on $100 million in annual revenue. The path there wasn’t a straight line. In the free-tier era, Railway was losing about $500K a month, and it switched the free tier off until owning its own bare-metal data centers made the economics work. The throughline since has been focus: say no to 90% of ideas, find the biggest problem each week, and move it forward, brick by brick.

    In this conversation, Jake walks through the operating system behind that leverage. Why he won’t look at how other companies solve a problem until Railway has tried its own answer. Why he thinks two co-founders is the worst number of co-founders. How a six-week onboarding built on trust, clarity, and judgment turns new hires into owners. And why his phone goes on do not disturb from Friday night to Sunday afternoon, because 996 buys 20% more cycles at best, but stillness is where the step-change ideas show up.

    Listen on YouTube, Spotify, and Apple Podcasts

    Jake Cooper is the founder and CEO of Railway, the cloud platform for deploying applications, databases, and agents, which he founded in 2020. Railway runs on its own bare-metal data centers, serves more than 2 million developers, and counts companies including MGM Resorts, Bilt, and TripAdvisor’s Cruise Critic among its customers. In January 2026, Railway raised a $100 million Series B, bringing its total funding to roughly $124 million. Before founding Railway, Cooper worked as a software engineer at Wolfram Research, Bloomberg, and Uber, where he scaled infrastructure for Jump bikes and scooters. He studied engineering at the University of Victoria in Canada.

    Where to find Jake Cooper:

    * Railway

    * X

    * LinkedIn

    Where to find Nakul:

    * Audacious Ventures

    * X

    * LinkedIn

    Where to find Audacious Ventures:

    * Website

    * LinkedIn

    In this conversation with Jake Cooper:

    00:00 Who is Jake Cooper?

    02:54 How did Railway survive losing $500K a month?

    06:01 What made Railway’s growth chart go vertical?

    09:45 Why won’t Jake look at how other companies solve problems?

    14:34 Is two the worst number of co-founders?

    20:04 How does a 40-person team get near $100M in ARR?

    22:41 Why does Railway say no to 90% of ideas?

    28:55 How do you compete for talent against the AI labs?

    32:25 What does a technical interview look like after Opus 4.5?

    35:34 Trust, clarity, judgment: how does Railway’s six-week onboarding work?

    44:59 What does HARD stand for, and which value costs the most?

    48:49 Why does Jake go dark from Friday night to Sunday?

    54:54 What breaks first in a world with 10,000x more software?

    59:49 Where does Railway play in two years?

    1:01:37 How has Jake had to grow as a CEO?

    1:09:29 Is burnout just an input-output mismatch?

    1:12:27 Why does Jake think most startup advice is overrated?

    Jake’s sharpest lines from this conversation:

    On studying other companies’ playbooks:

    “To me, it’s almost like cheating on your homework when you go and look at somebody else’s solution. You pollute your own brain with whatever that is.”

    On having a co-founder:

    “Two is awful. Do they make couples counselors for co-founders?”

    On being a solo founder:

    “I am the last and only person that picks up the phone. If somebody has a problem for me, it means that probably the whole rest of the org could not solve that problem.”

    On following conventional startup advice:

    “I think most startup advice is overrated, because you have to plot your own journey.”

    On taking weekends off:

    “There are massive step functions buried inside of everybody’s business that they can go and unlock by simply, what I would say, finding stillness.”

    On running a fully remote company:

    “It like never even really crossed my mind to like have this in person because remote allows us to pull the best people from literally every, every facet of the world.


    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com

    How Juicebox is building for the AI talent war | David Paffenholz (CEO) Sep 22, 2026
    Show notes

    David Paffenholz says Juicebox has not lost a single employee in two years, at a company that has grown from three people to ninety. He credits it to a formula: independence, visible impact, and real equity, what he calls the preconditions for a place where someone feels they can do their life’s work. That formula sits inside a deliberately intense culture: five days a week in the office, no exceptions, but explicitly not 996.

    Paffenholz co-founded the company in 2022 with Ishan Gupta, first as PeopleGPT, on a narrow bet: that the hardest part of recruiting was never the workflow, it was search, and that large language models would make search fundamentally different from what LinkedIn and Indeed had already built. That bet has taken Juicebox from $1.5 million in ARR with a three-person team to an $850 million valuation on an $80 million Series B, serving more than 5,000 customers from AI-native startups to large financial services and defense organizations, and positioning itself as the agent-native alternative to LinkedIn’s roughly $8 billion Talent Solutions business.

    In this conversation, David walks through why he thinks the “AI recruiter” hype mostly missed the point, how much autonomy he’s willing to give Juicebox’s own agents, why there are still zero engineering managers at a 90-person company, and what changed once he could no longer track what everyone was working on day to day. He’s candid about the calls he’s gotten wrong, including the MCP server he resisted and then had to reverse, and what he’d tell his 22-year-old-self who bet his company on a search bar.

    Listen on YouTube, Spotify, and Apple Podcasts

    David Paffenholz is the co-founder and CEO of Juicebox, the AI-native recruiting platform he built with co-founder Ishan Gupta out of Y Combinator’s Summer 2022 batch, first under the name PeopleGPT. Juicebox raised an $80 million Series B led by DST Global in 2026 at an $850 million valuation, with Sequoia Capital, Coatue, Y Combinator, and others also participating, and now serves more than 5,000 customers, from early-stage AI startups to large enterprises in financial services and defense. Before founding Juicebox at 22, Paffenholz worked at New Enterprise Associates and Moonfare and on international expansion at Snap Inc., and studied economics at Harvard University. He grew up in Germany. Juicebox has since opened an office in London and grown to roughly 90 employees without losing one in the past two years.

    Where to find David Paffenholz:

    * Juicebox

    * X

    * LinkedIn

    Where to find Nakul:

    * Audacious Ventures

    * X

    * LinkedIn

    Where to find Audacious Ventures:

    * Website

    * LinkedIn

    In this conversation with David Paffenholz:

    0:00 Who is David Paffenholz?

    2:42 Why did betting everything on search beat the “AI recruiter” hype?

    6:57 From search to copilot to agents: how has the product evolved?

    10:02 Why hasn’t LinkedIn already built this?

    11:34 What’s stopping OpenAI or Anthropic from just building this instead?

    13:14 How does Juicebox stay ahead as competitors ship just as fast?

    16:25 What made David’s first 60-second LinkedIn video actually work?

    18:12 “Message market fit” vs product market fit: what’s the real difference?

    19:12 What was the brutal six months after launch actually like?

    22:50 Why are large enterprises still slow to adopt AI recruiting?

    30:49 What are Juicebox’s only two company values?

    32:17 How does Juicebox mandate five days in office without going 996?

    35:17 How has Juicebox never lost an employee in two years?

    45:32 Does David think 90% of employees need to be “AI-pilled”?

    56:57 What happens when a candidate gets 240 outreaches and answers four?

    1:05:50 What was David’s biggest mistake as a first-time CEO?

    1:10:30 Quickfire: red flags, overrated advice, and Cursor’s hiring machine

    1:16:10 How is David thinking about kids and life at 25?

    David’s sharpest lines from this conversation:

    On the insight the whole company was built on:

    “Almost everything comes down to search. Are they finding the right talent, and are they bringing net new talent into their funnel?”

    On the difference between hype and traction:

    “Message market fit is when you have people signing up and starting to use the product. Product market fit is when they retain.”

    On staying narrow instead of building everything:

    “We want to stay narrow on sourcing. We want to help you find the best candidates, and do just that.”

    On empowering fast decisions:

    “Everyone is empowered to make those decisions, and it’s totally okay if someone gets them wrong.”

    On what makes people stay:

    “There’s this concept of being the place where someone feels that they can do their life’s work.”

    On why founders should trust their recruiters:

    “The recruiter is their ally in that process.”

    On the advice he’d give his earlier self:

    “I’d tell the earlier version of myself to be even more comfortable in being wrong and telling others that I was wrong.”


    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com

    $7B AI founder: "AI is not capable of replacing you right now" Sep 09, 2026
    Show notes

    In 2024, OpenAI asked its own investors to avoid funding five companies it saw as competitive threats: Anthropic, Elon Musk's xAI, Ilya Sutskever's Safe Superintelligence, the search engine Perplexity, and one enterprise AI company, Glean. Arvind Jain built Glean after a decade as a distinguished engineer at Google and after co-founding the data security company Rubrik, starting it in 2019, years before most of the world had heard of generative AI.

    –

    Glean is now valued at $7.2 billion, generates more than $300 million in annual recurring revenue, and employs roughly 1,500 people, one of the largest pure-play enterprise AI companies in the world. Its bet is that enterprises don't need Glean to build its own frontier model. They need it to be the context and intelligence layer that plugs into whichever model, Claude, GPT, Gemini, or an open source one, actually gets the job done.

    –

    In this conversation, Arvind walks through why he doesn't believe AI will let companies meaningfully shrink their workforce, even as it reshapes what people do all day. How Glean's own leaders, not just its engineers, are required to build their own AI agents, no exceptions. And why, after seven years running one of the most AI-native companies in the world, the feeling of having "arrived" still hasn't shown up.

    –

    Arvind Jain is the founder and CEO of Glean, an enterprise AI platform valued at $7.2 billion that he founded in 2019 after spending more than a decade at Google as a distinguished engineer, leading teams across Search, Maps, and YouTube. Before Glean, Jain co-founded Rubrik, the publicly traded cloud data security company, where he led R&D. Glean has raised more than $765 million from investors including Sequoia Capital, Kleiner Perkins, Lightspeed Venture Partners, ICONIQ, and Wellington Management, most recently a $150 million Series F in June 2025. In 2024, OpenAI reportedly asked its own investors not to fund Glean, placing it on a list alongside Anthropic, xAI, and Safe Superintelligence. Jain holds a BTech in computer science from the Indian Institute of Technology, Delhi, and a master's in computer science from the University of Washington.

    –

    Where to find Arvind Jain:

    • Glean

    • X

    • LinkedIn

    –

    Where to find Nakul:

    • Audacious Ventures

    • X

    • LinkedIn

    –

    Where to find Audacious Ventures:

    • Website

    • LinkedIn

    –

    In this conversation with Arvind Jain:

    00:00 Who is Arvind Jain?

    01:56 What is Glean's edge as OpenAI, Google, and Notion pile in?

    04:56 MCP vs. context graphs: why did Glean go its own way?

    07:56 What structural advantage does Glean claim over the frontier labs themselves?

    11:00 How does Glean stack up against AI-native platforms like Notion?

    12:38 What happens to the SaaS stack by 2027 and 2028?

    14:52 Is Glean an app, an agent platform, or core infrastructure?

    19:22 How much of Glean's use today is questions versus real agent work?

    20:52 What does a knowledge worker's life look like in three years?

    24:08 Why doesn't Arvind think AI will let companies shrink their workforce?

    27:32 How does Arvind self-serve strategy, talent, and customer insight with AI?

    33:19 Is every department at Glean AI-native, not just engineering?

    36:44 What did Arvind find flawed in the AI SDR dream?

    38:19 How has AI reshaped hiring at Glean, and who thrives there now?

    41:07 Are Glean's 1,500 employees secretly doing the work of 2,500?

    41:55 Why does Arvind say you never feel like you've "arrived"?

    45:38 What's Arvind's advice for anyone who wants his life?

    –

    Arvind's sharpest lines from this conversation:

    On why headcount survives AI:

    "Ultimately, the business success is indeed proportional to the human capital that you have inside the company."

    –

    On AI closing the skill gap:

    "Take a calculator. Does everyone know how to use it today equally well? I think that's what's gonna happen with AI."

    –

    On the real job of a CEO:

    "As a CEO, most of my job is understanding, and I think these are actually harder problems, frankly."

    –

    On AI SDRs and human judgment:

    "AI should be used as a tool, not something that replaces the entire human task. It can replace 90% of the task."

    –

    On spotting AI-written text:

    "My high school kids can tell you very quickly what text is written by AI and which one is not."

    –

    On why nothing feels defensible now:

    "Everything that you build, instead of it feeling like your moat or your IP, sometimes it feels like a liability, because you have to quickly get rid of it."

    –

    On what AI still can't do:

    "AI is not capable of replacing you right now. Let's be clear, it's not ready to replace even a single human today, no matter what job they do today."

    –

    On advice for someone starting out:

    "Work very, very hard until the very last day. You'll be building connections with the people who've worked with you, and your impressions always carry forward. That's the one that actually gives you those rewards."


    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com

    Inside Vercel's AI-era playbook: "Recursive Founder Mode" Aug 25, 2026
    Show notes

    Guillermo Rauch’s kindergarten teachers had a question for his parents: “What do you guys give this kid? He’s a freaking ball of energy.” Today Guillermo is at the gym every morning, has five kids with a sixth on the way, does Vercel’s customer support rotations himself, and measures his own keystrokes with an app he vibe coded. He is also the founder and CEO of one of the defining infrastructure companies of the AI era.

    –

    If you have built anything on the internet, you have probably touched his work. Guillermo created Socket.IO, co-created Next.js, the most popular React framework in the world, and founded Vercel, now valued at $9.3 billion with a revenue run rate of more than $500 million, powering frontends for OpenAI, Stripe, and Nike. The throughline of this episode is his answer to Paul Graham’s Founder Mode essay: founder mode doesn’t scale, so Vercel runs on what Guillermo calls Recursive Founder Mode, finding people who are founders at heart and making them the CEOs of their own products. It’s the machine that builds the machine.

    –

    In this conversation, Guillermo walks through what that looks like in practice. Why he is still involved in every hire at nearly 800 people, and why nobody at Vercel except security can stop a launch. How V, the internal agent the company runs on, replaced ticket queues and bent the headcount curve. What the new engineering meta skill is when models write the code. And the inner game: the energy budget, the lulls, and why he calls 996 rookie numbers.

    –

    Guillermo Rauch is the founder and CEO of Vercel, the AI cloud company behind Next.js, v0, the AI SDK, and the AI Gateway, valued at $9.3 billion following a $300 million Series F led by Accel and GIC in September 2025. Rauch created Socket.IO and Mongoose, two of the most widely used libraries in the JavaScript ecosystem, and co-created Next.js, the most popular React framework. Born in Lanús, Argentina, he taught himself to program, moved to San Francisco at 18, and co-founded LearnBoost and Cloudup, acquired by Automattic in 2013. He founded Vercel, originally called ZEIT, in 2015; the company now employs nearly 800 people and serves customers including OpenAI, Stripe, and Nike.

    –

    Where to find Guillermo Rauch:

    • Vercel

    • X

    • LinkedIn

    –

    Where to find Nakul:

    • Audacious Ventures

    • X

    • LinkedIn

    –

    Where to find Audacious Ventures:

    • Website

    • LinkedIn

    –

    In this conversation with Guillermo Rauch:

    00:00 Who is Guillermo Rauch?

    02:01 What is Recursive Founder Mode?

    07:28 Why did Vercel open source its playbook with skills.sh?

    10:14 What is a “work prompt” interview?

    14:33 Why is Guillermo still involved in every hire at nearly 800 people?

    18:17 What keeps founders at Vercel when seed money is everywhere?

    23:41 Do urgency and taste pull against each other?

    26:43 What is the new engineering meta skill?

    32:21 How does a 17-year-old show they’re exceptional today?

    35:47 Why does Vercel route the whole company through one agent?

    38:47 Which software survives the agent era?

    42:11 How has AI changed Guillermo’s job as CEO?

    51:39 Does Vercel even need executives anymore?

    54:40 If Guillermo started Vercel today, what would he build first?

    57:45 What’s the story behind v0?

    1:03:48 Are there still moats when anyone can build fast?

    1:11:24 How does a legendary coder learn the inner game of being a CEO?

    1:19:21 Where does Guillermo’s energy actually come from?

    1:23:07 Quickfire: overrated advice, Chrome, voice AI, Demo Fridays

    1:28:38 What does the journey actually require?

    –

    Guillermo’s sharpest lines from this conversation:

    On scaling founder mode:

    “The founder CEO can only go so far. You kind of want to build the machine that builds the machine.”

    –

    On agents being the first port of call:

    “If I DM you, it probably meant that my agent couldn’t figure it out.”

    –

    On AI and taste:

    “I think people sometimes create this false dichotomy between AI and taste. You know what’s tasteless is grabbing the model and having it output as it is.”

    –

    On why AI doesn’t write his tweets:

    “I think the best connection I’m gonna be able to make with you is if you get my legitimate, authentic farm-to-table next token from me, not from a machine.”

    –

    On working out consistently:

    “You have to spend energy to increase your energy budget.”


    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com

    How a first-time CEO is taking on Google: No process, no NPC hires, and extreme shipping velocity Aug 04, 2026
    Show notes

    Will Bryk was working as one of the first engineers at Cresta, writing a book about the history of civilization on the side, when the research started to feel absurd. “Google is great for surface-level investigations,” he says. “But it is not built to find every article on what people ate in medieval times across different regions of the world.” The frustration with accessibility of information went back to high school. He recalls thinking how ridiculous it is that we can split the atom and get to the moon, but still find it hard to understand what is happening at the border. To him, that’s an error in humanity.

    –

    Then GPT-3 arrived, and with it, the possibility of a different kind of search engine. Will and his college roommate Jeff Wang started Exa in 2021 with the lofty goal of building one better than Google. Five years on, Exa has raised $250 million at a $2.2 billion valuation led by a16z, its crawlers track over 500 billion URLs, and it powers search for Cursor, Cognition, HubSpot and more than 5,000 companies.

    –

    In this conversation, Will walks through how he runs the company making that bet. Why he gets genuinely upset when someone tries to introduce a process. What a non-playable character is and why Exa screens them out. Why the “bitter lesson” works on compute but not on people. And why a founder whose role models are Spider-Man and Ethan Hunt from Mission Impossible says he has not had a single thought about burnout in the past couple of years.

    –

    Listen on:

    • Spotify: https://open.spotify.com/show/5KorHDryscDzLwPkWEgAH1

    • Apple Podcasts: https://podcasts.apple.com/us/podcast/knuckle-up-with-nakul/id1893213920

    –

    Will Bryk is the co-founder and CEO of Exa, which builds web search infrastructure for AI agents. Exa’s search API powers Cursor, Cognition, HubSpot, OpenRouter and Monday.com, and the company says it serves more than 400,000 developers. Bryk co-founded Exa with Jeff Wang out of Y Combinator’s Summer 2021 batch, and the company raised its $250 million round from Andreessen Horowitz in May 2026. Before Exa he was one of the first engineers at Cresta, where he built real-time AI products. He studied computer science and physics at Harvard University, where he researched human-AI interaction and led the robotics club.

    –

    Where to find Will Bryk:

    • Exa: https://exa.ai

    • X: https://x.com/WilliamBryk

    • LinkedIn: https://www.linkedin.com/in/william-bryk

    –

    Where to find Nakul:

    • Audacious Ventures: https://www.audacious.co/

    • X: https://x.com/nakul

    • LinkedIn: https://www.linkedin.com/in/nakulmandan/

    –

    Where to find Audacious Ventures:

    • Website: https://www.audacious.co/

    • LinkedIn: https://www.linkedin.com/company/audaciousventures/

    –

    In this conversation with Will Bryk:

    00:00 Who is Will Bryk?

    01:49 Why do agents need a different search engine than humans?

    02:53 How can an independent search company survive the big labs?

    07:33 What does the internet look like when agents do the searching?

    10:19 How did writing a book on the history of civilization lead to Exa?

    15:39 Why does Exa hire first-principles thinkers, not rebels?

    18:05 What is a “non-playable character,” and why does Exa screen for it?

    19:49 How does Exa win engineers against the labs’ packages?

    21:30 Why does Will kill process “before it lays eggs”?

    26:27 Does the “bitter lesson” apply to humans?

    29:52 What breaks when a company outgrows a single room?

    34:47 Are there 100x and 1000x engineers now, not just 10x?

    37:32 Why should nothing at Exa ever take a month to ship?

    45:30 Where does Will’s drive actually come from?

    48:28 Why are Will’s role models fictional, not real?

    51:05 What does “We’ll figure it out” mean at Exa?

    54:05 Why do Will’s best thoughts happen at 2:00 AM?

    57:47 Quickfire: red flags, young founder myths, and Will’s mission impossible

    –

    Will’s sharpest lines from this conversation:

    On why information is the mission:

    “That to me is just an error in humanity. Why can’t they figure out how to share information in a normal way? Why is everything politicized? I always thought this was ridiculous, and I don’t accept it.”

    –

    On process:

    “I think you could solve a lot of problems with culture, not process.”

    –

    On the pace at Exa:

    “A month is an insane amount of time. Nothing should ever take a month to ship at Exa.”

    –

    On why his heroes are fictional:

    “It’s almost like an oxymoron for there to be a famous real superhero, because if you’re a real superhero, you’re anonymous.”

    –

    On what burnout actually is:

    “If you actually think about what burnout is, it’s wheels turning but not moving.”

    –

    On what he is still trying to solve:

    “Perfect alignment within the company, on what is most important and why this matters. This is my mission, if I choose to accept it.”

    –

    On what he screens out:

    “We really try to avoid non-playable characters. People who just go through life as if they’re on a stream and they have no agency over themselves.”


    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com

    0 → $1b in a year: The remarkable story of Handshake's refounding Jul 21, 2026
    Show notes

    At a Christmas party in December 2024, Garrett Lord met a researcher who told him about the challenges with model training. This researcher was working at a frontier AI lab. Two weeks later, Garrett’s company Handshake was recruiting STEM PhDs for that same lab. Fifteen months after that, Handshake AI had gone from zero to a billion dollars in gross annualized revenue, run by a founder who jokes he couldn’t spell reinforcement learning when he started.

    –

    Before that Christmas party, Garrett’s company Handshake was already huge. A decade of building had made it the career network for an entire generation: 18 million students and alumni, 1,600 schools, almost every company in the Fortune 500, and a valuation well north of $3 billion. Most founders would spend the next ten years protecting that. Instead, over the course of 2025, Garrett refounded the company around a business that was barely a year old. He moved his strongest people over, took a fully remote workforce to five days a week in office, watched around 100 people leave, and codified a value called Olympic Pace.

    –

    In this conversation, Garrett walks through the why and how of that transformation. How he incubated a new business inside a profitable one, and what he told his execs and board. Why he triages problems with red, yellow, green, and why he hasn’t upgraded a single exec. What the bear case on human data misses. And how he holds it together at home with a 10-month-old, a second baby on the way, and both in-laws going through cancer treatment.

    –

    Garrett Lord is the co-founder and CEO of Handshake, the career network he started in 2014 with Scott Ringwelski and Ben Christensen while studying computer science at Michigan Technological University. Handshake connects 18 million students and alumni across 1,600 schools with employers including almost every company in the Fortune 500, and was valued at $3.5 billion after its $200 million Series F in 2022. In 2025, Lord launched Handshake AI, which recruits students, alumni, and professionals from the network to produce post-training data, evaluations, and reinforcement learning environments for frontier AI labs; the business went from zero to $1 billion in gross revenue in about 15 months and has acquired eight companies. Handshake also runs upskilling and enterprise evaluation businesses on the same network, with offices in New York, San Francisco, and Bangalore.

    –

    Where to find Garrett Lord:

    * Handshake

    * X

    * LinkedIn

    –

    Where to find Nakul Mandan:

    * X

    * LinkedIn

    –

    Where to find Audacious Ventures:

    * Website

    * LinkedIn

    –

    In this conversation with Garrett Lord:

    00:00 Who is Garrett Lord?

    01:36 How did a Christmas party conversation spark Handshake AI?

    11:59 How do you tell your execs and board you’re refounding the company?

    18:18 What keeps A players motivated in the core business?

    22:22 Olympic Pace: why did around 100 team members leave Handshake?

    27:02 What broke first going zero to a billion in a year?

    31:45 How do you protect quality when 85% of the company is new?

    39:36 Why hasn’t Garrett upgraded a single exec?

    49:00 What does the bear case on human data get wrong?

    53:30 How do you make accounting verifiable enough for reinforcement learning?

    1:00:08 Will enterprises leave the labs for open source?

    1:07:13 What does all this mean for knowledge workers?

    1:08:51 The inner game: how is Garrett holding it all together?

    1:14:22 What’s the mission in this new chapter?

    1:18:27 Will vertical AI apps survive the frontier labs?

    1:21:23 Quickfire: red flags, overrated advice, jobs of the future

    –

    Garrett’s sharpest lines from this conversation:

    On how much AI knowledge Garrett has learned from scratch:

    “I couldn’t spell reinforcement learning when I started this business.”

    –

    On Olympic Pace:

    “If you just compound and stack day after day after day and give it your best, great things will happen. That’s been the story of my life and the story of this business.”

    –

    On how long human data lasts:

    “There will be human data for as long as humans are needed in the economy.”

    –

    On who understands this market:

    “There’s a big difference between what the MBAs say and what the researchers say.”

    –

    On the future of enterprise work:

    “I think the future of a lot of employees in enterprises actually looks more akin to being a Waymo driver in your job.”

    –

    On no rearview mirror:

    “I spend 0% of my time celebrating any of our success.”


    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com

    The new marketing playbook: “Marketing Engineers” and agents as the audience Jul 07, 2026
    Show notes

    James Cadwallader and his co-founder Dylan Babbs were working six days a week in an office before they had a company, or even an idea. James would drag Dylan into their coworking space on Saturdays, ban laptops, and fill a whiteboard with post-it notes; for a stretch, the leading idea was lithium mining. He calls it hardcore from day minus one. Twenty-one months after launch, Profound is a $1 billion company with more than 700 enterprise customers and over 13% of the Fortune 500 on the platform.

    The thesis: marketing is about to change more than it has in the last 25 years. The old internet playbook was built for humans browsing the web. The next one is being built for AI agents interpreting it. When ChatGPT recommends a product, it doesn't just give you a link. It opines, 3,000 characters at a time, and it’s a marketers job to drive what’s in those characters. James watched the last platform shift from inside the room, building Kyra and running creative for Nike, Unilever, and Prada while social and TikTok ate the old marketing playbook. Now he's building the infrastructure for this one.

    In this conversation, James maps the new marketing operating system. Why you're no longer marketing to John Smith but to John Smith's agent. The “Marketing Engineer”, a role Profound coined and Google has already hired for. Why ideas become the bottleneck when content costs nothing to produce. And the culture James calls the best product Profound has built: six days a week in office, and you can still leave at 6pm without anyone batting an eyelid.

    Listen on:

    • Spotify: https://open.spotify.com/show/5KorHDryscDzLwPkWEgAH1

    • Apple Podcasts: https://podcasts.apple.com/us/podcast/knuckle-up-with-nakul/id1893213920

    James Cadwallader is the co-founder and CEO of Profound, the AI visibility platform that helps brands measure and shape how AI assistants like ChatGPT, Gemini, and Perplexity talk about them. Profound serves enterprise customers including Target, Walmart, and U.S. Bank. Cadwallader started Profound in New York City with co-founder Dylan Babbs after the two met at the startup incubator South Park Commons. Before Profound, he co-founded Kyra, a London-based creator marketing company.

    Where to find James Cadwallader:

    • Profound: https://www.tryprofound.com/

    • X: https://x.com/thejamescad

    • LinkedIn: https://www.linkedin.com/in/jsca/

    Where to find Nakul:

    • Audacious Ventures: https://www.audacious.co/

    • X: https://x.com/nakul

    • LinkedIn: https://www.linkedin.com/in/nakulmandan/

    Where to find Audacious Ventures:

    • Website: https://www.audacious.co/

    • LinkedIn: https://www.linkedin.com/company/audaciousventures/

    In this conversation with James Cadwallader:

    00:00 Who is James Cadwallader?

    03:56 What happens when ChatGPT recommends your product?

    08:33 How do you market to machines instead of people?

    11:10 How is this different to SEO?

    15:00 What is a Marketing Engineer?

    17:23 What is the antidote to AI slop?

    20:56 When marketing copy is free, what's the new bottleneck?

    24:25 Can Profound get bigger than Adobe and Salesforce?

    28:04 Why does Profound's marketing team have only eight people?

    33:57 How did Profound become a unicorn in 18 months?

    37:22 Post-it notes and lithium mining: how did Profound begin?

    40:49 Which AI tools actually run Profound day to day?

    47:29 Why does James call culture the best product Profound has built?

    53:54 What breaks when a startup crosses 250 people?

    1:01:12 What is James most paranoid about?

    1:04:44 Quickfire: workflows to kill, AI-era brands, business books, AI SDRs

    1:06:00 What's the recommended 90-day plan for a Fortune 500 CMO?

    James's sharpest lines from this conversation...

    On the new question for every brand:

    "In the old world of search, it was just this question of how do I rank? And in this new world, the question is not just do I show up, but how do I show up?"

    On the antidote to AI slop:

    "The antidote to slop, from my experience, is more context."

    On what AI still can't know:

    "There are things that you know about Audacious right now that Chat and Claude simply don't know... You're an API between reality and AI at this point."

    On his ambition for Profound:

    "I'm never going to have another opportunity like this. This is it. This is my shot. So yeah, I'm kind of planning on trying to take it all the way."

    On enterprise speed:

    "We work with giant Fortune 10 brands who are a lot faster than you'd expect."

    On culture:

    "I've said a few times that our culture is the best product we've built. It's the product that I'm most proud of."

    On who thrives at Profound:

    "We look for masters of craft and people that are default hard working. That's what they do if left to their own devices."

    On what he tells the team at all-hands:

    "I'm very curious to see who in this room sticks it out when things actually get hard. Because right now we're playing the game on easy mode."


    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com

    Building a $5b company without 996 Jun 23, 2026
    Show notes

    Most founders get more stressed as the company gets bigger. Immad Akhund has spent years engineering the opposite. “I’ve tried to make it so that the pressure kind of goes down as success goes up, which I think is relatively rare,” he says. “If you’re more successful, why are you more stressed about it?” This may be surprising coming from someone running one of the most loved fintechs of this generation. But Immad has reached this point through a deliberate operating philosophy that he shares in this discussion.Mercury serves around 300,000 customers, runs at a $650 million annualized run rate, and has been profitable for four years straight. One in three US startups banks with it, and in April 2026 the company won conditional approval to establish Mercury Bank, N.A. Immad has done all of it on his own terms: anti-996, still remote-first while Silicon Valley snapped back to fully in person, and hiring for curiosity and humility. The throughline is that he optimized early to be a founder for life, not for a sprint.In this conversation, Immad walks me through how that philosophy actually runs a 1,200-person company. Why 996 may not make you more productive. What Mercury’s famous curiosity interview is really testing. Why he killed one-on-ones after listening to Jensen Huang. How AI has turned the disruption of banking further in Mercury’s favor. And why, three startups in, the thing he would tell his younger self is to build something he would actually love to exist.Listen on YouTube, Spotify, and Apple PodcastsImmad Akhund is the co-founder and CEO of Mercury, the fintech banking platform founded in 2017 that serves around 300,000 businesses and runs at a $650 million annualized run rate. In April 2026, Mercury received conditional approval from the Office of the Comptroller of the Currency to establish Mercury Bank, N.A., and the company subsequently raised $200 million at a $5.2 billion valuation. Before Mercury, Akhund co-founded Heyzap, a mobile developer platform that went through Y Combinator and sold for $45 million in 2016, and earlier co-founded Clickpass. He has served as a part-time partner at Y Combinator and is a prolific angel investor backing more than 350 startups, including Airtable, Substack, and Deel. He was born in Pakistan and raised in the UK before moving to the United States.In this conversation with Immad Akhund:00:00 Who is Immad Akhund?01:53 Is culture just the founder’s personality externalized?07:53 Is 996 actually less productive?13:14 Why is Mercury still remote-first when Silicon Valley went back?15:52 How did Immad hire Mercury’s first ten people?20:33 What is Mercury’s famous “curiosity interview”?25:06 How do you hold the hiring bar at 1,200 people?28:48 What does Immad’s day-to-day look like?34:10 How do you know when an exec is no longer right for the job?37:32 Why does Mercury run on small, autonomous product teams?40:27 What breaks when a company runs purely on metrics?47:03 How is AI changing Mercury?54:09 What does becoming a chartered bank actually change?56:19 How did the SVB collapse end up helping Mercury?1:03:40 What does psyche management look like 20 years in?1:11:19 What does it mean to be at the founder “bonus levels”?1:15:21 Quickfire: overrated traits, AI blind spots, and being proven wrong1:17:52 What would Immad tell his 25-year-old self?Where to find Immad:* Mercury* X* LinkedInWhere to find Nakul:* X* LinkedInWhere to find Audacious Ventures:* Website* LinkedInImmad’s sharpest lines from this conversation:On pressure and success:“I’ve tried to make it so that the pressure kind of goes down as success goes up, which I think is actually relatively rare. If you’re more successful, why are you more stressed about it?”On the math of a 996 day:“The extra two hours, was that really 20% more productive? I will be shocked if it was 20% more productive. It’s maybe 5% more productive.”On where culture actually comes from:“It does start with founder personalities, but then you try to structure that, try to encourage that internally, then you hire against it. Then it becomes a self-perpetuating thing, and it also shows up in the product and how you talk to customers.”On why he killed one-on-ones:“I’ve never found one-on-ones help. One-on-ones is just an avenue for them to try to sell themselves. You need to create avenues where you have visibility into what that team is doing.”On holding execs accountable:“I don’t think execs can have excuses. I think that’s the job, to deliver on that.”On why AI favors Mercury:“I highly doubt Bank of America has an MCP. We are extremely well situated for that because we are a technology company, and that’s just what we do.”On reinvention:“I love change. I live for change. Change is the main thing I want in life.”On his advice to his 25-year-old self:“Build something that you would really love for it to exist, rather than being too spreadsheet about it.”Full Transcript: Immad Akhund on Knuckle UpImmad Akhund:9-9 is 12 hours. The extra two hours, was that really 20% more productive? I will be shocked if it was 20% more productive. If you have five employees and you hire a sixth employee, that’s 20% more productive.You’re probably a little less creative if you’re not doing anything else in your life. I have my best ideas when I’m on a flight or driving somewhere. Sometimes these decisions or these ideas are actually worth 10x more than an extra few hours of work.I started as entrepreneur. I loved it, but I just wanted to survive.We got to a billion dollar valuation in 2021. At that point, which is like, I would say I really got into the bonus levels on this game where I was like, “I don’t even know what my next goal is.” I’ve tried to make it so the pressure goes down as success goes up, which is I think actually relatively rare.If you’re more successful, why are you more stressed about it?Nakul Mandan:Immad Akhund has built one of the most loved FinTechs of this generation. Mercury serves 300,000 customers and is at a $650 million annualized run rate. One in three US startups banks with them. The company has been profitable for four straight years, and as of last month, they have conditional approval to become Mercury Bank. But what’s interesting is that Immad has accomplished all of this on his own terms. He’s anti-996. He’s still remote first at a time when Silicon Valley has bounced back to fully in-person. He hires for traits most growth-stage companies don’t even look for. He said, “It’s dangerous when everything has to be driven by metrics.” And he said openly that he’s optimized early on to be a founder for life and not for a sprint. Today we talked to Immad about how he runs Mercury, the operating philosophy that got him here and whether that philosophy holds up as Mercury becomes a bank and AI-shaped company and a business serving companies well beyond the tech ecosystem. Knuckle up.Immad, welcome to the show.Immad Akhund:Ah, thanks for having me.Nakul Mandan:Yeah. So I want to start with something you’ve said that actually cuts through a lot of the culture theater in Silicon Valley. You’ve said that the culture is about the founder’s personality, not about some values doc, not about some rituals. The founder’s personality externalized. And I was wondering as I was preparing for this, that works for 10 people, 100 people company, maybe even stretch it to a 500 people company, but at the scale at which Mercury is today, 1000-plus people, does it still work?Immad Akhund:Oh, yeah. 100%. I mean, I think I often talk to people who talk about culture, but I think they don’t know what it means, and I think it’s like an ill-defined word and I’m an engineer, so I hate ill-defined words. So I really struggled with it for a long time. I was like, “Is it like having beers in the fridge and going, ‘That’s what it was,’ or is it like what programming language you choose, et cetera?” So I think there are probably some people mean culture and they mean something else. I think the easiest way to define culture that is very definitive and means something and you can measure it and all that is what are the personalities of the people you hire, what are the personalities that you encourage, what are the types of traits you encourage, kind of thing.You kind of have to decide that very early on because what happened in my previous company is I didn’t really understand that. So we had a bunch of salespeople that kind of ended up dominating the culture because they were the loudest voice in the room and we didn’t really have a counterculture to fix that. So it was fine, but it wasn’t like the type of company I wanted to build with Mercury. So we sat down and I think there was only four people and we’re like, “Okay, what are the personalities that we really cared about?” And for us it was kind of product-minded, humble, helpful people that were kind of curious and at that time we didn’t like meetings so we were like no process, go build things kind of people.And so we wrote that down and we tried to measure against it. We had interviews like every engineer, everyone we did product interviews with, and we would try to test people for, okay, are they high ego? So there’s a bunch of things that followed from that and we have a bunch of things within the company that encouraged that behavior. We pick one thing, like we have a channel called Grateful and people at the company, like every day there’s multiple posts where people are like, “Oh, I’m really grateful to X and Y because they helped launch this project or whatever it is.” A lot of that behavior is organic. I didn’t make that channel, it just came across. But I think it’s important and I also think different personalities can work.I always think of Uber as an example of a very competitive, high eco kind of culture, at least in the Travis days. Obviously they built a very successful company doing that. It doesn’t work for my personality. I also think it doesn’t work for the product we’re building. Yeah, maybe it could work, but I think Mercury is a very customer-centric kind of product where we’re very transparent and open with our customers and we try to be. That authenticity is part of the reason I think Mercury is successful. It does start with founder personalities, but then you try to structure that, try to encourage that internally, then you hire against it, then it becomes like a self-perpetuating thing and it also shows up in the product and how you talk to customers.Nakul Mandan:Does it potentially lead to also though having a lot of the same personality in the... Can a different personality come in into the company?Immad Akhund:Well, you need a little bit of just different energy sometimes, but it can sometimes ruin things. Sometimes you let someone who is a bad fit come as a leader. I mean, I think it’s especially an issue with exec level. I think at IC level, you can have a lot more variance and I don’t think it spoils things too much. But at a leadership level, if you have someone and then they hire people against them and for whatever reason that clashes with the rest of the company and then you can have a team that’s in a silo that... It can lead to a lot of bad things, and we are very careful at the exec level where we take a lot longer hiring and we try to test against our culture fit quite a bit. But it’s not like... You never have 100% conformity and you don’t necessarily want that either. You need enough of it that you are really being true to that culture and not letting it deteriorate.Nakul Mandan:What about the other side of it, which is the founder also evolves in the journey. Mercury has come such a long way. The Immad that started Mercury versus the Immad who is today. So has the culture evolved with your personality?Immad Akhund:We end up assessing it probably once a year and changing it once a year.Nakul Mandan:So it is a living doc.Immad Akhund:It is a living doc. Change is difficult to some extent because you don’t want to be drastically, “Now we believe in something completely different and opposite.” So what we tend to do is evaluate it from like, okay, the set of cultural things we have, are they serving us? Yeah, take that. We literally used to have one, like no meetings. I can’t remember the exact phrasing, but sometimes the fastest way to get to a decision is a meeting.Nakul Mandan:Oh, was it no weekly meeting?Immad Akhund:No, it was a very anti-meetings-like phrase. It was like, “We don’t like meetings.” And it was fine. When there’s 10 people and you’re all in a room, it doesn’t matter. But it wasn’t serving us and we got rid of that. And so there’s some that you remove and then there’s some that you’re like, “Hey, we really want to encourage this behavior.” You have to also try to shift culture by creating something. So I think one of the more recent one was we were like, “Focus on outcomes,” and then we created a bunch of things to... We try to create a bunch of rituals around the culture as well. So it’s like we’re focused on outcomes. So what are the outcomes we focus on? How do we drive that? How do we encourage it and celebrate when people are doing the right thing? How do we put in the performance management process so someone’s going to get promotion? Part of it is like, okay, maybe they did all the right things, but the outcomes didn’t happen and how do we measure all of that?So it has to be something that shifts over time. I think to some extent my personality changes over time, but not that much. I mean, I guess I started Mercury 80 years ago when I was 33. There hasn’t been drastic changes in personality. I mean, I learn a lot, but yeah, the core stuff is still the core.Nakul Mandan:In Silicon Valley these days, there’s a lot of talk about 996 constantly. It’s gone towards fully about intense cultures and you’re on the other side. You’ve built a $650 million revenue business. Obviously you have scaled in a way that very, very few people in history have scaled businesses. Can you talk about what does the 996 culture get wrong? What’s your though about this?Immad Akhund:From day zero we’ve had... We work hard, but it’s normally five days a week, whatever, 9:00 to 6:00 or something like that. We don’t have a religion around it. I have a family. I already had two kids before I started Mercury, now I have three, and I really see entrepreneurship as a long-term thing. I’ve done it for the last 20 years. I want to keep doing it for another 20 years. So I really want to do it in a way that it fits into my life. I used to be a 996 person, not because I was like, “Oh, I like 996.” It was just like I didn’t have kids, I wasn’t married. I woke up in the morning and I started... I was more than 996. I woke up at 9:00 and then I just worked till midnight being like, “Maybe you go out for dinner, maybe you don’t, and then who cares if it’s the weekend because you’re not doing anything.” That’s basically how I ran the first few years of my startup life.I think to some extent there’s been a shift with AI where being young is no longer a problem in the sense that with B2B SaaS, if you were young and you don’t have the experience to see B2B problems, it was hard to build a B2B SaaS company, which is the previous wave in the startup world. Now with AI, everything you’ve learned is probably wrong and you have to kind of reinvent it.Nakul Mandan:It’s liability problems.Immad Akhund:Yeah, it’s maybe even a liability. And also there’s just a lot of people out there that just want to play with the technology that are young, that... I started startups when I was 22. It’s the best time to do a startup. You have no obligations, you just need enough money to survive with the least amount of lifestyle cost. Yeah, there’s a big wave of young people. So I think that’s part of the shift that they don’t care.And I found personally when I was young and I was sitting on my computer all day, the reality is I wasn’t productive all day. I was on Twitter and I’m a pretty…

    Full show notes at the publisher

    Startup lessons Silicon Valley won’t teach you | Cameron McCord (Co-founder of Nominal) Jun 09, 2026
    Show notes

    Cameron McCord spent 484 days underwater. As a submarine officer in the US Navy, he learned to run a reactor in a space where the crew sees you 24/7, even brushing your teeth, and where there is no "later" to sort out a disagreement. He still calls the Navy the single biggest influence on how he leads. After the submarine came Capitol Hill as a Navy congressional liaison, then early Anduril, then Saildrone, then a stint in venture at Lux Capital. Each one was a deliberate move toward starting a company.

    –

    That company is Nominal, a connected software suite that is changing how the world tests and operates hardware. Three years in, Nominal is valued at $1 billion, has raised $155 million in ten months, and counts four of the five largest defense contractors as customers. The team has grown from around 40 people to 170 in a year, across offices in LA, Austin, New York, DC, and now London.

    –

    In this conversation, Cameron walks through the operating playbook underneath that growth. Why he still interviews everyone and looks for people who are "three layers deep." What it means to "earn the right to stand the night watch." How he imports intentional ambiguity from early Anduril and a critique culture from the submarine. And where physical AI is actually going.

    –

    In this conversation with Cameron McCord:

    00:00 Who is Cameron McCord?

    01:34 What did 484 days underwater teach him about leadership?

    10:36 How do you "earn the right to stand the night watch"?

    16:28 What was so special about Anduril’s culture?

    28:39 What is the "power of ambiguity"?

    31:29 How does Cameron think about recruiting?

    37:39 Can you recruit “killers” who are also low ego?

    46:50 What was the broken old way of testing hardware?

    50:50 How do you actually crack selling to the government?

    55:12 How did Nominal land four of the five largest defense primes?

    1:01:33 What does "physical AI" actually mean?

    1:18:14 What is Cameron still working on in his inner game?

    1:23:22 Quickfire: military movies, leadership books, and a favorite office?

    1:25:07 What advice would Cameron give to his 25-year-old self?

    –

    Cameron's sharpest lines from this conversation...

    On why the weakest link defines the team:

    "Even if you're the person turning a wrench on a pump, if you don't do your job, the team could be at risk, because everything has to come together."

    On what he recruits for:

    "The biggest gift, and frankly the thing you look for in talent, in recruiting, is people that are fit to stand the night watch… a safe pair of hands."

    On asking a team to do the impossible:

    "It is always worth going the extra mile to draw the thread between the impossible task you're asking someone to do and the outcome for a customer."

    On what it takes to win:

    "Do one thing and do it really, really well… in practice, you need to do something 10 times better than the current way."

    On the inner game of leadership:

    "Being comfortable in your own head is so powerful, and it’s the biggest gift I can give to Nominal."

    On a mantra from his submarine captain:

    "Stress is the body preparing you for greatness."

    –

    Where to find Cameron:

    • Nominal

    • X

    • LinkedIn

    –

    Where to find Nakul:

    • Audacious Ventures

    • X

    • LinkedIn

    –

    Where to find Audacious Ventures:

    • Website

    • LinkedIn


    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com

    Business used to be go karting. Now it's Formula 1. May 27, 2026
    Show notes

    Akshay Kothari has spent most of his time at Notion trying to put himself out of a job. His move, repeated for years, is to run at whatever the company's biggest unsolved problem is, build the system around it, hire someone great to own it, and then remove himself. In 2023 the approach left him, a co-founder of a multibillion-dollar company, with zero direct reports and a calendar wide open to think.

    That instinct fits the company he helps run. Notion built itself like an art project: profitable, still largely owned by its founders and employees, raising money only when there was a real reason to, and kept deliberately small, around 1,200 people running a business at public scale. For years its core was a system of record, a modern editor and database that people genuinely loved and built their work inside. Then AI changed what people expect software to do, and Notion decided to reinvent the product rather than wait to be replaced.

    In this conversation, Akshay walks through how Notion pulled that off: the stretch he calls the swamp of despair, when its AI agent failed four times before it worked; why the company stopped trying to make the model fit its product and started fitting the product to the model; and how it dissolved the line between its AI team and everyone else until there was nobody left who wasn't building with AI. The bet landed. AI moved from a defensive play to a real driver of growth, and Notion's growth rate has climbed for over a year, with the most recent quarter running about 50% above where it was a year earlier. As Akshay frames it, the business went from go-karting to Formula 1, and now the company has to rewire how it drives.

    Listen on...

    • Spotify: https://open.spotify.com/show/5KorHDryscDzLwPkWEgAH1

    • Apple Podcasts: https://podcasts.apple.com/us/podcast/knuckle-up-with-nakul/id1893213920

    Akshay Kothari is the co-founder and chief operating officer of Notion, where he has built and scaled functions from support and sales to marketing and finance, alongside co-founders Ivan Zhao (CEO) and Simon Last. Before Notion, he co-founded Pulse, a news-reading app that won an Apple Design Award, reached 30 million users, and was acquired by LinkedIn for $90 million in 2013.

    Where to find Akshay Kothari...

    • Notion: https://www.notion.com/

    • X: https://x.com/akothari

    • LinkedIn: https://www.linkedin.com/in/akothari

    Where to find Nakul...

    • Audacious Ventures: https://www.audacious.co/

    • X: https://x.com/nakul

    • LinkedIn: https://www.linkedin.com/in/nakulmandan/

    Where to find Audacious Ventures...

    • Website: https://www.audacious.co/

    • LinkedIn: https://www.linkedin.com/company/audaciousventures/

    In this conversation with Akshay Kothari...

    00:00 Who is Akshay Kothari?

    01:27 What were Notion's core founding principles?

    06:20 Which early cultural principles scaled, and which broke?

    08:22 How did Notion hire its first employees, and where did they come from?

    11:48 How does hiring work now that the founders can't meet everyone?

    14:35 Why does Akshay, as COO, prefer to have zero direct reports?

    19:05 How do Ivan, Simon, and Akshay divide the work?

    21:07 Does Notion's intentionality ever conflict with speed?

    25:25 What should other founders steal from Notion's culture?

    28:11 When did AI become a reason to rethink the whole product?

    30:44 Why were the early AI years a "swamp of despair"?

    36:05 How do you push AI across a huge product without losing the user?

    39:25 Does Notion buy its AI DNA or build it?

    40:44 Should Notion be afraid of OpenAI, Anthropic, and fast copycats?

    46:58 What's hardest about the reinvention, and what does "meet the LLM" mean?

    52:42 Is Notion AI-native in every function yet?

    54:36 Are Notion's engineers still writing code, and how has engineering changed?

    1:01:07 Once building is cheap, what's the new bottleneck?

    1:02:39 How is AI reshaping sales, marketing, and support?

    1:09:07 How many agents run inside Notion, and who builds them?

    1:11:28 How has recruiting changed for the AI era?

    1:13:48 What still worries Akshay about Notion's future?

    1:15:22 Quickfire: admired founders, books, overrated AI advice, and Akshay’s superpower

    1:19:42 What should a $50M pre-AI company do in the next 90 days?

    Akshay's sharpest lines from this conversation...

    On putting himself out of a job:

    "Ivan calls me a stem cell. I go there and build something, then I get out of it."

    On meeting the model where it is:

    "You really have to stop trying to fit the LLM with what you have, and you have to fit what you have to the other."

    On what AI is really for:

    "The best companies are just raising their ambitions. It's less about efficiency and more about, can each person be way more productive?"

    On just how much AI changed business:

    "We cannot take the way we were go-karting and apply it to Formula One."

    On disrupting yourself before the market does:

    "You have to disrupt yourself to where the business is going. You can kind of do it to yourself before someone else does it to you."


    This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com

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